N-((6-trifluoromethylpyrimidin-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamides

ABSTRACT

N-((6-Trifluoromethylpyrimidin-2-yl)- aminocarbonyl)-2-carboalkoxybenzenesulfonamides of the general formula Ia ##STR1## where the substituents have the following meanings: R 1  is hydrogen or halogen; 
     R 2  is hydrogen, C 1  -C 5  -alkyl, C 3  -C 4  -alkenyl, C 3  -C 4  -alkynyl, C 1  -C 5  -haloalkyl, C 3  -C 5  -alkoxyalkyl, C 3  -C 5  -haloalkoxyalkyl or C 5  -C 6  -cycloalkyl, 
     R 3  is hydrogen, C 1  -C 2  -alkyl, allyl, propargyl or C 1  -C 5  -alkoxy, 
     R 4  is halogen, C 1  -C 2  -alkyl, C 1  -C 3  -alkylthio or C 1  -C 3  -alkylamino, 
     R 3  not denoting hydrogen or C 1  -C 2  -alkyl when R 4  is C 1  -C 2  -alkyl, and their environmentally tolerated salts, processes for their manufacture, and their use.

The present invention relates to N-((6-trifluoromethylpyrimidin-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamides of the general formula Ia ##STR2## where R¹ is hydrogen or halogen, R² is hydrogen, C₁ -C₅ -alkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -alkynyl, C₁ -C₅ -haloalkyl, C₃ -C₅ -alkoxyalkyl, C₃ -C₅ -haloalkoxyalkyl or C₅ - or C₆ -cycloalkyl, R³ is hydrogen, C₁ - or C₂ -alkyl, allyl, propargyl or C₁ -C₅ -alkoxy and R⁴ is halogen, C₁ - or C₂ -alkyl, C₁ -C₃ -alkylthio or C₁ -C₃ -alkylamino, and R³ is not hydrogen or C₁ - or C₂ -alkyl when R⁴ is C₁ - or C₂ -alkyl, and their environmentally compatible salts, and N-((6-trifluoromethylpyrimidin-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamides of the general formula Ib ##STR3## where R⁵ is hydrogen, fluorine or chlorine, R⁶ is C₁ -C₃ -alkyl, R⁷ is hydrogen or methyl and R⁸ is hydrogen or C₁ -or C₂ -alkoxy.

The present invention relates in particular to N-((6-trifluoromethylpyrimidin-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamides of the general formulae Ia and Ib in which R² and R⁶, respectively, are methyl, and those in which R⁴ and R⁸, respectively, are chlorine, methoxy or methylthio.

The present invention furthermore relates to processes for the preparation of the compounds Ia and Ib and herbicides which contain these compounds.

U.S. Pat. No. 4,169,719 discloses sulfonylureas having a herbicidal action. Furthermore, EP-A 7687 describes herbicidal sulfonylureas whose general formula embraces the N-((6-trifluoromethylpyrimidin-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamides of the general formula Ib, defined at the outset. However, the known agents do not meet all requirements with respect to specific activity against undesirable plants and toleration by crops.

It is an object of the present invention to find and synthesize sulfonylureas which have advantageous properties compared with the known active ingredients of this class of herbicides.

We have found that this object is achieved by the N-((6-trifluoromethylpyrimidinyl-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamides of the general formulae Ia and Ib, defined at the outset.

A sulfonylurea of the formula Ia or Ib is obtained, for example, by reacting a corresponding compound of the formula IIa or IIb, respectively, ##STR4## with a corresponding compound of the formula IIIa or IIIb, respectively, ##STR5## at a temperature of up to 120° C., preferably from 10° to 100° C., which is conventionally used for organic reactions. The reaction can be carried out under atmospheric or superatmospheric pressure, continuously or batchwise.

The sulfonylureas of the formulae Ia and Ib can also be obtained by reacting a corresponding sulfonamide of the formula IVa or IVb, respectively, ##STR6## with a corresponding phenyl carbamate of the formula Va or Vb, respectively, ##STR7## advantageously in the presence of a tertiary amine at a temperature of up to 120° C., preferably from 10° to 100° C., which is conventionally used for organic reactions.

The sulfonylureas of the formulae Ia and Ib may furthermore be obtained by reacting a corresponding phenyl carbamate of the formula VIa or VIb, respectively, ##STR8## with a corresponding amine of the formula IIIa or IIIb, respectively, ##STR9## advantageously in the presence of a tertiary amine at a temperature of up to 120° C., preferably from 10° to 100° C., which is conventionally used for organic reactions.

Solvents or diluents are advantageously used for the reactions. Examples of suitable solvents are halohydrocarbons, in particular chlorohydrocarbons, e.g. tetrachloroethylene, 1,1,2,2- and 1,1,1,2-tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, chloronaphthalene, dichloronaphthalene, carbon tetrachloride, 1,1,1- and 1,1,2-trichloroethane, trichloroethylene, pentachloroethane, o-, m- and p-difluorobenzene, 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, chlorobenzene, fluorobenzene, bromobenzene, iodobenzene, o-, m- and p-dichlorobenzene, o-, p- and m-dibromobenzene, o-, m- and p-chlorotoluene and 1,2,4-trichlorobenzene; ethers, e.g. ethyl propyl ether, methyl tert.-butyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, diisopropyl ether, anisole, phenetole, cyclohexyl methyl ether, diethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, thioanisole and β,β'-dichlorodiethyl ether; nitrohydrocarbons, such as o-, m- and p-chloronitrobenzene and o-nitrotoluene; nitriles, such as acetonitrile, butyronitrile, isobutyronitrile, benzonitrile and m-chlorobenzonitrile; aliphatic and cycloaliphatic hydrocarbon, e.g. heptane, pinane, nonane, o-, m-and p-cymene, gasoline fractions boiling within a range of from 70° to 190° C., cyclohexane, methylcyclohexane, decalin, petroleum ether, hexane, naphtha, 2,2,4-trimethylpentane, 2,2,3-trimethylpentane and octane; esters, e.g. ethyl acetate, ethyl acetoacetate and isobutyl acetate; amides, e.g. formamide, methylformamide and dimethylformamide; ketones, e.g. acetone and methyl ethyl ketone, and mixtures of these. The solvent is advantageously used in an amount of from 100 to 2000, preferably from 200 to 700, % by weight, based on the starting materials II, IV or VI.

The compounds III or V required for the reaction are generally used in a roughly stoichiometric ratio. The intermediates II, IV or VI may be initially taken in a diluent and the intermediate III or V then added.

However, the process for the preparation of the novel compounds is advantageously carried out by initially taking the intermediate III or V and adding the intermediate II or IV or VI.

The reactions are generally complete in the course of from 20 minutes to 24 hours at from 0° to 120° C., preferably from 10° to 100° C., in particular from 20° to 80° C.

In the reactions which can be advantageously affected by the presence of a tertiary amine as a reaction accelerator, for example pyridine, 2,4- or 2,6-lutidine, 2,4,6-collidine, α,β-picoline, p-dimethylaminopyridine, 1,4-diaza[2.2.2]bicyclooctane (DABCO) or 1,8-diazabicyclo[5.4.0]undec-7-ene are used, in an amount of not more than 1 mole per mole of intermediate IV or VI.

If the sulfonylureas are in the form of an acid, the salt can be prepared by reaction with a stoichiometric amount of an aqueous base or of a metal alcoholate, in the presence or absence of an organic solvent. Another possibility is alkaline hydrolysis of the corresponding esters.

The end products are obtained from the particular reaction mixtures in a conventional manner, for example after distilling off solvents or directly by filtration under suction. The remaining residue can furthermore be washed with water or a dilute acid to remove basic impurities. However, it is also possible for the residue to be dissolved in a water-miscible solvent and the solution washed in the manner described. The desired end products are obtained in this case in pure form; if necessary, they can be purified by recrystallization or chromatography.

The compounds of the formulae II, III, IV, V and VI which are required as intermediates can be prepared by reactions known from the literature. For example, the preparation of the starting materials III is described by Gershon (H. Gershon, A. T. Grefig and A. A. Scala, J. Heterocycl. Chem. 20 (1983) 219), or the starting materials can be prepared similarly to the methods described there.

With regard to the biological activity, preferred sulfonylureas of the formula Ia are those in which

R¹ is hydrogen or halogen, such as fluorine, chlorine, bromine or iodine, in particular hydrogen, fluorine, chlorine or bromine,

R² is hydrogen, alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, in particular methyl, ethyl, propyl, 1-methylethyl or 1-methylpropyl, alkenyl, such as 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl or 3-butenyl, in particular 2-propenyl or 2-butenyl, alkynyl, such as 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl or 3-butynyl, in particular 2-propynyl or 2-butynyl, haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl, in particular difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, alkoxyalkyl, such as 2-methoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2-methoxy-1-methylethyl, ethoxymethyl, 2-ethoxyethyl, 2-ethoxypropyl, 3-ethoxypropyl, 2-ethoxy-1-methylethyl or 1-ethoxy-1-methylethyl, in particular methoxyethyl or ethoxyethyl, haloalkoxyalkyl, such as difluoromethoxyethyl, trifluoromethoxyethyl, chlorodifluoromethoxyethyl, dichlorofluoromethoxyethyl, 1-fluoroethoxyethyl, 2-fluoroethoxyethyl, 2,2-difluoroethoxyethyl, 1,1,2,2 -tetrafluoroethoxythyl, 2,2,2-trifluoroethoxyethyl, 2-chloro-1,1,2-trifluoroethoxyethyl or pentafluoroethoxyethyl, in particular trifluoromethoxyethyl, or cycloalkyl, such as cyclopentyl or cyclohexyl,

R³ is hydrogen, methyl, ethyl, allyl, propargyl or alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, in particular hydrogen, methyl, allyl, propargyl, methoxy or ethoxy, and

R⁴ is halogen as stated for R¹, in particular fluorine, chlorine or bromine, alkylthio, such as methylthio, ethylthio, propylthio or 1-methylethylthio, in particular methylthio, ethylthio or 1-methylethylthio, or alkylamino, such as methylamino, ethylamino, propylamino or 1-methylethylamino, in particular methylamino or ethylamino.

With regard to the biological activity, particularly preferred sulfonylureas of the formula Ib are those in which R⁵ is hydrogen, fluorine or chlorine, R⁶ is, in particular, methyl or ethyl, R⁷ is hydrogen or methyl and R⁸ is hydrogen, methoxy or ethoxy.

Regarding the biological activity, specific examples of herbicidal sulfonylureas of the general formula Ia are summarized in the table below.

                  TABLE                                                            ______________________________________                                          ##STR10##                     Ia                                              R.sup.1                                                                               R.sup.2      R.sup.3      R.sup.4                                       ______________________________________                                         H      CH.sub.3     H            Cl                                            H      C.sub.2 H.sub.5                                                                             H            Cl                                            H      n-C.sub.3 H.sub.7                                                                           H            Cl                                            H      n-C.sub.4 H.sub.9                                                                           H            Cl                                            H      i-C.sub.3 H.sub.7                                                                           H            Cl                                            H      sec-C.sub.4 H.sub.9                                                                         H            Cl                                            H      CH.sub.2 CHCH.sub.2                                                                         H            Cl                                            H      CH.sub.2 CCH H            Cl                                            H      CH.sub.2 CH.sub.2 Cl                                                                        H            Cl                                            H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            Cl                                            H      cyclohexyl   H            Cl                                            H      CH.sub.3     H            OCH.sub.3                                     H      C.sub.2 H.sub.5                                                                             H            OCH.sub.3                                     H      n-C.sub.3 H.sub.7                                                                           H            OCH.sub.3                                     H      n-C.sub.4 H.sub.9                                                                           H            OCH.sub.3                                     H      i-C.sub.3 H.sub.7                                                                           H            OCH.sub.3                                     H      sec-C.sub.4 H.sub.9                                                                         H            OCH.sub.3                                     H      CH.sub.2 CHCH.sub.2                                                                         H            OCH.sub.3                                     H      CH.sub.2 CCH H            OCH.sub.3                                     H      CH.sub.2 CH.sub.2 Cl                                                                        H            OCH.sub.3                                     H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            OCH.sub.3                                     H      cyclohexyl   H            OCH.sub.3                                     H      CH.sub.3     H            OC.sub.2 H.sub.5                              H      C.sub.2 H.sub.5                                                                             H            OC.sub.2 H.sub.5                              H      n-C.sub.3 H.sub.7                                                                           H            OC.sub.2 H.sub.5                              H      n-C.sub.4 H.sub.9                                                                           H            OC.sub.2 H.sub.5                              H      i-C.sub.3 H.sub.7                                                                           H            OC.sub.2 H.sub.5                              H      sec-C.sub.4 H.sub.9                                                                         H            OC.sub.2 H.sub.5                              H      CH.sub.2 CHCH.sub.2                                                                         H            OC.sub.2 H.sub.5                              H      CH.sub.2 CCH H            OC.sub.2 H.sub.5                              H      CH.sub.2 CH.sub.2 Cl                                                                        H            OC.sub.2 H.sub.5                              H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            OC.sub.2 H.sub.5                              H      cyclohexyl   H            OC.sub.2 H.sub.5                              H      CH.sub.3     H            O-i-C.sub.3 H.sub.7                           H      C.sub.2 H.sub.5                                                                             H            O-i-C.sub.3 H.sub.7                           H      n-C.sub.3 H.sub. 7                                                                          H            O-i-C.sub.3 H.sub.7                           H      n-C.sub.4 H.sub.9                                                                           H            O-i-C.sub.3 H.sub.7                           H      i-C.sub.3 H.sub.7                                                                           H            O-i-C.sub.3 H.sub.7                           H      sec-C.sub.4 H.sub.9                                                                         H            O-i-C.sub.3 H.sub.7                           H      CH.sub.2 CHCH.sub.2                                                                         H            O-i-C.sub.3 H.sub.7                           H      CH.sub.2CCH  H            O-i-C.sub.3 H.sub.7                           H      CH.sub.2 CH.sub.2 Cl                                                                        H            O-i-C.sub.3 H.sub.7                           H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            O-i-C.sub.3 H.sub.7                           H      cyclohexyl   H            O-i-C.sub.3 H.sub.7                           H      CH.sub.3     H            O-n-C.sub.3 H.sub.7                           H      C.sub.2 H.sub.5                                                                             H            O-n-C.sub.3 H.sub.7                           H      n-C.sub.3 H.sub.7                                                                           H            O-n-C.sub.3 H.sub.7                           H      n-C.sub.4 H.sub.9                                                                           H            O-n-C.sub.3 H.sub.7                           H      i-C.sub.3 H.sub.7                                                                           H            O-n-C.sub.3 H.sub.7                           H      sec-C.sub.4 H.sub.9                                                                         H            O-n-C.sub.3 H.sub.7                           H      CH.sub.2 CHCH.sub.2                                                                         H            O-n-C.sub.3 H.sub.7                           H      CH.sub.2CCH  H            O-n-C.sub.3 H.sub.7                           H      CH.sub.2 CH.sub.2 Cl                                                                        H            O-n-C.sub.3 H.sub.7                           H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            O-n-C.sub.3 H.sub.7                           H      cyclohexyl   H            O-n-C.sub.3 H.sub.7                           H      CH.sub.3     H            NHCH.sub.3                                    H      C.sub.2 H.sub.5                                                                             H            NHCH.sub.3                                    H      n-C.sub.3 H.sub.7                                                                           H            NHCH.sub.3                                    H      n-C.sub.4 H.sub.9                                                                           H            NHCH.sub.3                                    H      i-C.sub.3 H.sub.7                                                                           H            NHCH.sub.3                                    H      sec-C.sub.4 H.sub.9                                                                         H            NHCH.sub.3                                    H      CH.sub.2 CHCH.sub.2                                                                         H            NHCH.sub.3                                    H      CH.sub.2 CCH H            NHCH.sub.3                                    H      CH.sub.2 CH.sub.2 Cl                                                                        H            NHCH.sub.3                                    H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            NHCH.sub.3                                    H      cyclohexyl   H            NHCH.sub.3                                    H      CH.sub.3     H            SCH.sub.3                                     H      C.sub.2 H.sub.5                                                                             H            SCH.sub.3                                     H      n-C.sub.3 H.sub.7                                                                           H            SCH.sub.3                                     H      n-C.sub.4 H.sub.9                                                                           H            SCH.sub.3                                     H      i-C.sub.3 H.sub.7                                                                           H            SCH.sub.3                                     H      sec-C.sub.4 H.sub.9                                                                         H            SCH.sub.3                                     H      CH.sub.2 CHCH.sub.2                                                                         H            SCH.sub.3                                     H      CH.sub.2 CCH H            SCH.sub.3                                     H      CH.sub.2 CH.sub.2 Cl                                                                        H            SCH.sub.3                                     H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            SCH.sub. 3                                    H      cyclohexyl   H            SCH.sub.3                                     H      CH.sub.3     H            SC.sub.2 H.sub.5                              H      C.sub.2 H.sub.5                                                                             H            SC.sub.2 H.sub.5                              H      n-C.sub.3 H.sub.7                                                                           H            SC.sub.2 H.sub.5                              H      n-C.sub.4 H.sub.9                                                                           H            SC.sub.2 H.sub.5                              H      i-C.sub.3 H.sub.7                                                                           H            SC.sub.2 H.sub.5                              H      sec-C.sub.4 H.sub.9                                                                         H            SC.sub.2 H.sub.5                              H      CH.sub.2 CHCH.sub.2                                                                         H            SC.sub.2 H.sub.5                              H      CH.sub.2 CCH H            SC.sub.2 H.sub.5                              H      CH.sub.2 CH.sub.2 Cl                                                                        H            SC.sub.2 H.sub.5                              H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            SC.sub.2 H.sub.5                              H      cyclohexyl   H            SC.sub.2 H.sub.5                              H      n-C.sub.3 H.sub.7                                                                           H            SC.sub.3 H.sub.7                              H      CH.sub.3     CH.sub.3     Cl                                            H      C.sub.2 H.sub.5                                                                             CH.sub.3     Cl                                            H      n-C.sub.3 H.sub.7                                                                           CH.sub.3     Cl                                            H      n-C.sub.4 H.sub.9                                                                           CH.sub.3     Cl                                            H      i-C.sub.3 H.sub.7                                                                           CH.sub.3     Cl                                            H      sec-C.sub.4 H.sub.9                                                                         CH.sub.3     Cl                                            H      CH.sub.2 CHCH.sub.2                                                                         CH.sub.3     Cl                                            H      CH.sub.2 C CH                                                                               CH.sub.3     Cl                                            H      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.3     Cl                                            H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.3     Cl                                            H      cyclohexyl   CH.sub.3     Cl                                            H      CH.sub.3     CH.sub.3     OCH.sub.3                                     H      C.sub.2 H.sub.5                                                                             CH.sub.3     OCH.sub.3                                     H      n-C.sub.3 H.sub.7                                                                           CH.sub.3     OCH.sub.3                                     H      n-C.sub.4 H.sub.9                                                                           CH.sub.3     OCH.sub.3                                     H      i-C.sub.3 H.sub.7                                                                           CH.sub.3     OCH.sub.3                                     H      sec-C.sub.4 H.sub.9                                                                         CH.sub.3     OCH.sub.3                                     H      CH.sub.2 CHCH.sub.2                                                                         CH.sub.3     OCH.sub.3                                     H      CH.sub.2 CCH CH.sub.3     OCH.sub.3                                     H      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.3     OCH.sub.3                                     H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.3     OCH.sub.3                                     H      cyclohexyl   CH.sub.3     OCH.sub.3                                     H      CH.sub.3     CH.sub.3     NHCH.sub.3                                    H      C.sub.2 H.sub.5                                                                             CH.sub.3     NHCH.sub.3                                    H      n-C.sub.3 H.sub.7                                                                           CH.sub.3     NHCH.sub.3                                    H      n-C.sub.4 H.sub.9                                                                           CH.sub.3     NHCH.sub.3                                    H      i-C.sub.3 H.sub.7                                                                           CH.sub.3     NHCH.sub.3                                    H      sec-C.sub.4 H.sub.9                                                                         CH.sub.3     NHCH.sub.3                                    H      CH.sub.2 CHCH.sub.2                                                                         CH.sub.3     NHCH.sub.3                                    H      CH.sub.2 CCH CH.sub.3     NHCH.sub.3                                    H      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.3     NHCH.sub.3                                    H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.3     NHCH.sub.3                                    H      cyclohexyl   CH.sub.3     NHCH.sub.3                                    H      CH.sub.3     OCH.sub.3    Cl                                            H      C.sub.2 H.sub.5                                                                             OCH.sub.3    Cl                                            H      n-C.sub.3 H.sub.7                                                                           OCH.sub.3    Cl                                            H      n-C.sub.4 H.sub.9                                                                           OCH.sub.3    Cl                                            H      i-C.sub.3 H.sub.7                                                                           OCH.sub.3    Cl                                            H      sec-C.sub.4 H.sub.9                                                                         OCH.sub.3    Cl                                            H      CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3    Cl                                            H      CH.sub.2 CCH OCH.sub.3    Cl                                            H      CH.sub.2 CH.sub.2 Cl                                                                        OCH.sub.3    Cl                                            H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 OCH.sub.3    Cl                                            H      cyclohexyl   OCH.sub.3    Cl                                            H      CH.sub.3     OCH.sub.3    OCH.sub.3                                     H      C.sub.2 H.sub.5                                                                             OCH.sub.3    OCH.sub.3                                     H      n-C.sub.3 H.sub.7                                                                           OCH.sub.3    OCH.sub.3                                     H      n-C.sub.4 H.sub.9                                                                           OCH.sub.3    OCH.sub.3                                     H      i-C.sub.3 H.sub.7                                                                           OCH.sub.3    OCH.sub.3                                     H      sec-C.sub.4 H.sub.9                                                                         OCH.sub.3    OCH.sub.3                                     H      CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3    OCH.sub.3                                     H      CH.sub.2 CCH OCH.sub.3    OCH.sub.3                                     H      CH.sub.2 CH.sub.2 Cl                                                                        OCH.sub.3    OCH.sub.3                                     H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 OCH.sub.3    OCH.sub.3                                     H      cyclohexyl   OCH.sub.3    OCH.sub.3                                     H      CH.sub.3     OCH.sub.3    CH.sub.3                                      H      C.sub.2 H.sub.5                                                                             OCH.sub.3    CH.sub.3                                      H      n-C.sub.3 H.sub.7                                                                           OCH.sub.3    CH.sub.3                                      H      n-C.sub.4 H.sub.9                                                                           OCH.sub.3    CH.sub.3                                      H      i-C.sub.3 H.sub.7                                                                           OCH.sub.3    CH.sub.3                                      H      sec-C.sub.4 H.sub.9                                                                         OCH.sub.3    CH.sub.3                                      H      CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3    CH.sub.3                                      H      CH.sub.2 CCH OCH.sub.3    CH.sub.3                                      H      CH.sub.2 CH.sub.2 Cl                                                                        OCH.sub.3    CH.sub.3                                      H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 OCH.sub.3    CH.sub.3                                      H      cyclohexyl   OCH.sub.3    CH.sub.3                                      H      CH.sub.3     OCH.sub.3    NHCH.sub.3                                    H      C.sub.2 H.sub.5                                                                             OCH.sub.3    NHCH.sub.3                                    H      n-C.sub.3 H.sub.7                                                                           OCH.sub.3    NHCH.sub.3                                    H      n-C.sub.4 H.sub.9                                                                           OCH.sub.3    NHCH.sub.3                                    H      i-C.sub.3 H.sub.7                                                                           OCH.sub.3    NHCH.sub.3                                    H      sec-C.sub.4 H.sub.9                                                                         OCH.sub.3    NHCH.sub.3                                    H      CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3    NHCH.sub.3                                    H      CH.sub.2 CCH OCH.sub.3    NHCH.sub.3                                    H      CH.sub.2 CH.sub.2 Cl                                                                        OCH.sub.3    NHCH.sub.3                                    H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 OCH.sub.3    NHCH.sub.3                                    H      cyclohexyl   OCH.sub.3    NHCH.sub.3                                    H      CH.sub.3     CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      C.sub.2 H.sub.5                                                                             CH.sub.2 CHCH.sup.2                                                                         Cl                                            H      n-C.sub.3 H.sub.7                                                                           CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      n-C.sub.4 H.sub.9                                                                           CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      i-C.sub.3 H.sub.7                                                                           CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      sec-C.sub.4 H.sub.9                                                                         CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      CH.sub.2 CHCH.sub.2                                                                         CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      CH.sub.2 CCH CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      cyclohexyl   CH.sub.2 CHCH.sub.2                                                                         Cl                                            H      CH.sub.3     CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      C.sub.2 H.sub.5                                                                             CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      n-C.sub.3 H.sub.7                                                                           CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      n-C.sub.4 H.sub.9                                                                           CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      i-C.sub.3 H.sub.7                                                                           CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      sec-C.sub.4 H.sub.9                                                                         CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      CH.sub.2 CHCH.sub.2                                                                         CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      CH.sub.2 CCH CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      cyclohexyl   CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3                                     H      CH.sub.3     CH.sub.2 CHCH.sub.2                                                                         CH.sub.3                                      H      C.sub.2 H.sub.5                                                                             CH.sub.2 CHCH.sub.2                                                                         CH.sub.3                                      H      n-C.sub.3 H.sub.7                                                                           CH.sub.2 CHCH.sub.2                                                                         CH.sub.3                                      H      n-C.sub.4 H.sub.9                                                                           CH.sub.2 CHCH.sub.2                                                                         CH.sub.3                                      H      i-C.sub.3 H.sub.7                                                                           OCH.sub.3    CH.sub.3                                      H      sec-C.sub.4 H.sub.9                                                                         OCH.sub.3    CH.sub.3                                      H      CH.sub.2 CHCH.sub.2                                                                         OCH.sub.3    CH.sub.3                                      H      CH.sub.2 CCH OCH.sub.3    CH.sub.3                                      H      CH.sub.2 CH.sub.2 Cl                                                                        OCH.sub.3    CH.sub.3                                      H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 OCH.sub.3    CH.sub.3                                      H      cyclohexyl   OCH.sub.3    CH.sub.3                                      H      CH.sub.3     CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      C.sub.2 H.sub.5                                                                             CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      n-C.sub.3 H.sub.7                                                                           CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      n-C.sub.4 H.sub.9                                                                           CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      i-C.sub.3 H.sub.7                                                                           CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      sec-C.sub.4 H.sub.9                                                                         CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      CH.sub.2 CHCH.sub.2                                                                         CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      CH.sub.2 CCH CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    H      cyclohexyl   CH.sub.2 CHCH.sub.2                                                                         NHCH.sub.3                                    Cl     CH.sub.3     H            Cl                                            Cl     C.sub.2 H.sub.5                                                                             H            Cl                                            Cl     n-C.sub.3 H.sub.7                                                                           H            Cl                                            Cl     n-C.sub.6 H.sub.9                                                                           H            Cl                                            Cl     i-C.sub.3 H.sub.7                                                                           H            Cl                                            Cl     sec-C.sub.4 H.sub.9                                                                         H            Cl                                            Cl     CH.sub.2 CHCH.sub.2                                                                         H            Cl                                            Cl     CH.sub.2 CCH H            Cl                                            Cl     CH.sub.2 CH.sub.2 Cl                                                                        H            Cl                                            Cl     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            Cl                                            Cl     cyclohexyl   H            Cl                                            Cl     CH.sub.3     H            OCH.sub.3                                     Cl     C.sub.2 H.sub.5                                                                             H            OCH.sub.3                                     Cl     n-C.sub.3 H.sub.7                                                                           H            OCH.sub.3                                     Cl     n-C.sub.4 H.sub.9                                                                           H            OCH.sub.3                                     Cl     i-C.sub.3 H.sub.7                                                                           H            OCH.sub.3                                     Cl     sec-C.sub.4 H.sub.9                                                                         H            OCH.sub.3                                     Cl     CH.sub.2 CHCH.sub.2                                                                         H            OCH.sub.3                                     Cl     CH.sub.2 CCH H            OCH.sub.3                                     Cl     CH.sub.2 CH.sub.2 Cl                                                                        H            OCH.sub.3                                     Cl     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            OCH.sub.3                                     Cl     cyclohexyl   H            OCH.sub.3                                     Cl     CH.sub.3     CH.sub.3     Cl                                            Cl     C.sub.2 H.sub.5                                                                             CH.sub.3     Cl                                            Cl     n-C.sub.3 H.sub.7                                                                           CH.sub.3     Cl                                            Cl     n-C.sub.4 H.sub.9                                                                           CH.sub.3     Cl                                            Cl     i-C.sub. 3 H.sub.7                                                                          CH.sub.3     Cl                                            Cl     sec-C.sub.4 H.sub.9                                                                         CH.sub.3     Cl                                            Cl     CH.sub.2 CHCH.sub.2                                                                         CH.sub.3     Cl                                            Cl     CH.sub.2 CCH CH.sub.3     Cl                                            Cl     CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.3     Cl                                            Cl     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.3     Cl                                            Cl     cyclohexyl   CH.sub.3     Cl                                            Cl     CH.sub.3     CH.sub.3     OCH.sub.3                                     Cl     C.sub.2 H.sub.5                                                                             CH.sub.3     OCH.sub.3                                     Cl     n-C.sub.3 H.sub.7                                                                           CH.sub.3     OCH.sub.3                                     Cl     n-C.sub.4 H.sub.9                                                                           CH.sub.3     OCH.sub.3                                     Cl     i-C.sub.3 H.sub.7                                                                           CH.sub.3     OCH.sub.3                                     Cl     sec-C.sub.4 H.sub.9                                                                         CH.sub.3     OCH.sub.3                                     Cl     CH.sub.2 CHCH.sub.2                                                                         CH.sub.3     OCH.sub.3                                     Cl     CH.sub.2 CCH CH.sub.3     OCH.sub.3                                     Cl     CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.3     OCH.sub.3                                     Cl     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.3     OCH.sub.3                                     Cl     cyclohexyl   CH.sub.3     OCH.sub.3                                     F      CH.sub.3     H            Cl                                            F      C.sub.2 H.sub.5                                                                             H            Cl                                            F      n-C.sub.3 H.sub.7                                                                           H            Cl                                            F      n-C.sub.4 H.sub.9                                                                           H            Cl                                            F      i-C.sub.3 H.sub.7                                                                           H            Cl                                            F      sec-C.sub.4 H.sub.9                                                                         H            Cl                                            F      CH.sub.2 CHCH.sub.2                                                                         H            Cl                                            F      CH.sub.2 CCH H            Cl                                            F      CH.sub.2 CH.sub.2 Cl                                                                        H            Cl                                            F      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            Cl                                            F      cyclohexyl   H            Cl                                            F      CH.sub.3     H            OCH.sub.3                                     F      C.sub.2 H.sub.5                                                                             H            OCH.sub.3                                     F      n-C.sub.3 H.sub.7                                                                           H            OCH.sub.3                                     F      n-C.sub.4 H.sub.9                                                                           H            OCH.sub.3                                     F      i-C.sub.3 H.sub.7                                                                           H            OCH.sub.3                                     F      sec-C.sub.4 H.sub.9                                                                         H            OCH.sub.3                                     F      CH.sub.2 CHCH.sub.2                                                                         H            OCH.sub.3                                     F      CH.sub.2 CCH H            OCH.sub.3                                     F      CH.sub.2 CH.sub.2 Cl                                                                        H            OCH.sub.3                                     F      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H            OCH.sub.3                                     F      cyclohexyl   H            OCH.sub.3                                     F      CH.sub.3     H            SCH.sub.3                                     F      CH.sub.3     CH.sub.3     Cl                                            F      C.sub.2 H.sub.5                                                                             CH.sub.3     Cl                                            F      n-C.sub.3 H.sub.7                                                                           CH.sub.3     Cl                                            F      n-C.sub.4 H.sub.9                                                                           CH.sub.3     Cl                                            F      i-C.sub.3 H.sub.7                                                                           CH.sub.3     Cl                                            F      sec-C.sub.4 H.sub. 9                                                                        CH.sub.3     Cl                                            F      CH.sub.2 CHCH.sub.2                                                                         CH.sub.3     Cl                                            F      CH.sub.2 CCH CH.sub.3     Cl                                            F      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.3     Cl                                            F      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.3     Cl                                            F      cyclohexyl   CH.sub.3     Cl                                            F      CH.sub.3     CH.sub.3     OCH.sub.3                                     F      C.sub.2 H.sub.5                                                                             CH.sub.3     OCH.sub.3                                     F      n-C.sub.3 H.sub.7                                                                           CH.sub.3     OCH.sub.3                                     F      n-C.sub.4 H.sub.9                                                                           CH.sub.3     OCH.sub.3                                     F      i-C.sub.3 H.sub.7                                                                           CH.sub.3     OCH.sub.3                                     F      sec-C.sub.4 H.sub.9                                                                         CH.sub.3     OCH.sub.3                                     F      CH.sub.2 CHCH.sub.2                                                                         CH.sub.3     OCH.sub.3                                     F      CH.sub.2 CCH CH.sub.3     OCH.sub.3                                     F      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.3     OCH.sub.3                                     F      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.3     OCH.sub.3                                     F      cyclohexyl   CH.sub.3     OCH.sub.3                                     ______________________________________                                    

The N-((6-trifluoromethylpyrimidin-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamides of the general formulae Ia and Ib, or herbicidal agents containing them, and the environmentally tolerated salts of alkali metals and alkaline earth metals, combat injurious plants excellently without damaging crop plants - an effect which is particularly apparent at low application rates. They may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible.

The compounds Ia and Ib are suitable for the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct. Examples of inert additives are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc.

Aqueous formulations may be prepared from emulsion concentrates, pastes, dispersions, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octyphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by weight of active ingredient.

The active ingredients may be formulated for instance as follows:

I. 90 parts by weight of compound no. 1.012 is mixed with 10 parts by weight of N-methyl-alpha-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 1.005 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

III. 20 parts by weight of compound no. 1.017 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

IV. 20 parts by weight of compound no. 1.012 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

V. 20 parts by weight of compound no. 1.010 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained containing 0.1% by weight of the active ingredient.

VI. 3 parts by weight of compound no. 1.009 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

VII. 30 parts by weight of compound no. 2.001 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 20 parts by weight of compound no. 2.009 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

The active ingredients may be applied pre- or postemergence. If certain crop plants tolerate the active ingredients less well, application techniques may be used in which the herbicidal agents are sprayed from suitable equipment in such a manner that the leaves of sensitive crop plants are if possible not touched, and the agents reach the soil or the unwanted plants growing beneath the crop plants (post-directed, lay-by treatment).

The application rates depend on the objective to be achieved, the time of the year, the plants to be combated and their growth stage, and are from 0.001 to 5.0, preferably 0.005 to 1.0, kg of active ingredient per hectare.

In view of the number of application methods possible, the compounds according to the invention, or agents containing them, may be used in a further large number of crops for removing unwanted plants. The following crops are given by way of example:

    ______________________________________                                         Botanical name         Common name                                             ______________________________________                                         Allium cepa            onions                                                  Ananas comosus         pineapples                                              Arachis hypogaea       peanuts                                                                        (groundnuts)                                            Asparagus officinalis  asparagus                                               Avena sativa           oats                                                    Beta vulgaris spp. altissima                                                                          sugarbeets                                              Beta vulgaris spp. rapa                                                                               fodder beets                                            Beta vulgaris spp. esculenta                                                                          table beets,                                                                   red beets                                               Brassica napus var. napus                                                                             rapeseed                                                Brassica napus var. napobrassica                                                                      swedes                                                  Brassica napus var. rapa                                                                              turnips                                                 Brassica rapa var. silvestris                                                  Camellis sinensis      tea plants                                              Carthamus tinctorius   safflower                                               Carya illinoinensis    pecan trees                                             Citrus limon           lemons                                                  Citrus maxima          grapefruits                                             Citrus reticulata      mandarins                                               Citrus sinensis        orange trees                                            Coffea arabica (Coffea canephora,                                                                     coffee plants                                           Coffea liberica)                                                               Cucumis melo           melons                                                  Cucumis sativus        cucumbers                                               Cynodon dactylon       Bermudagrass                                            Daucus carota          carrots                                                 Elais guineensis       oil palms                                               Fragaria vesca         strawberries                                            Glycine max            soybeans                                                Gossypium hirsutum (Gossypium arboreum,                                                               cotton                                                  Gossypium herbaceum, Gossypium vitifolium)                                     Helianthus annuus      sunflowers                                              Helianthus tuberosus   Jerusalem artichoke                                     Hevea brasiliensis     rubber plants                                           Hordeum vulgare        barley                                                  Humulus lupulus        hops                                                    Ipomoea batatas        sweet potatoes                                          Juglans regia          walnut trees                                            Lactuca sativa         lettuce                                                 Lens culinaris         lentils                                                 Linum usitatissimum    flax                                                    Lycopersicon lycopersicum                                                                             tomatoes                                                Malus spp.             apple trees                                             Manihot esculenta      cassava                                                 Medicago sativa        alfalfa (lucerne)                                       Mentha piperita        peppermint                                              Musa spp.              banana plants                                           Nicotiana tabacum (N. rustica)                                                                        tobacco                                                 Olea europaea          olive trees                                             Oryza sativa           rice                                                    Panicum miliaceum      millet                                                  Phaseolus lunatus      limabeans                                               Phaseolus mungo        mungbeans                                               Phaseolus vulgaris     snapbeans, green                                                               beans, dry beans                                        Pennisetum glaucum     pearl millet                                            Petroselinum crispum spp. tuberosum                                                                   parsley                                                 Picea abies            Norway spruce                                           Abies alba             fir trees                                               Pinus spp.             pine trees                                              Pisum sativum          English peas                                            Prunus avium           cherry trees                                            Prunus domestica       plum trees                                              Prunus dulcis          almond trees                                            Prunus persica         peach trees                                             Pyrus communis         pear trees                                              Ribes sylvestre        redcurrants                                             Ribes uva-crispa       gooseberries                                            Ricinus communis       castor-oil plants                                       Saccharum officinarum  sugar cane                                              Secale cereale         rye                                                     Sesamum indicum        sesame                                                  Solanum tuberosum      Irish potatoes                                          Sorghum bicolor (s. vulgare)                                                                          sorghum                                                 Sorghum dochna         sorgo                                                   Spinacia oleracea      spinach                                                 Theobroma cacao        cacao plants                                            Trifolium pratense     red clover                                              Triticum aestivum      wheat                                                   Triticum durum         durum wheat                                             Vaccinium corymbosum   blueberries                                             Vaccinium vitis-idaea  cranberries                                             Vicia faba             tick beans                                              Vigna sinensis (V. unguiculata)                                                                       cow peas                                                Vitis vinifera         grapes                                                  Zea mays               Indian corn, sweet                                                             corn, maize                                             ______________________________________                                    

To increase the spectrum of action and to achieve synergistic effects, the sulfonylureas of the formula Ia and Ib may be mixed and applied together with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable components are diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acids, phenyloxy- or heteroaryloxy-phenylpropionic acids and salts, esters and amides thereof, etc.

It may also be useful to apply the novel compounds of the formula Ia and Ib, either alone or in combination with other herbicides, in admixture with other crop protection agents, e.g., agents for combating pests or phytopathogenic fungi or bacteria. The compounds may also be mixed with solutions of mineral salts used to remedy nutritional or trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

SYNTHESIS EXAMPLE Methyl 2-(((4-methoxy-6-trifluoromethyl-1,3-pyrimidin-2-yl)-aminocarbonyl)-aminosulfonyl)-benzoate

At room temperature, 6.5 g of methyl 2-(isocyanatosulfonyl)-benzoate in 50 ml of absolute acetonitrile was introduced over a period of 10 minutes, with stirring and under a nitrogen blanket, to a suspension of 5.2 g of 2-amino-4-methoxy-6-trifluoromethylpyrimidine in 100 ml of absolute acetonitrile. The temperature rose by 10° C. After the reaction mixture had been stirred for 13 hours at 70° C., it was evaporated down and the residue was taken up in dichloromethane. The organic phase was washed once with 1N hydrochloric acid and once with 1N sodium hydroxide solution, dried with sodium sulfate and filtered. After the solvent had been stripped off, there was obtained 9.7 g of the title compound having a melting point of 150°-151° C.

The compounds given in the following tables were prepared by modifying the above example.

    ______________________________________                                         Active ingredient table 1                                                       ##STR11##                     Ia                                              Compound                                                                       No.      R.sup.1                                                                              R.sup.2    R.sup.3                                                                            R.sup.4   mp(°)                           ______________________________________                                         1.001    H     CH.sub.3   H   Cl        176-177                                1.002    H     CH.sub.3   H   OCH(CH.sub.3).sub.2                                                                      170-173                                1.003    H     CH.sub.3   H   NHCH.sub.3                                                                               115-117                                1.004    H     CH.sub.3   H   SCH.sub.3 155-157                                1.005    H     CH.sub.3   H   SCH.sub.2 CH.sub.3                                                                       71-73                                  1.006    H     CH.sub.2 CH.sub.3                                                                         H   SCH.sub.3 114-117                                1.007    H     (CH.sub.2).sub.2 CH.sub.3                                                                 H   SCH.sub.3 146-148                                1.008    H     (CH.sub.2).sub.2 CH.sub.3                                                                 H   S(CH.sub.2).sub.2 CH.sub.3                                                               146-148                                1.009    F     CH.sub.3   H   Cl        86-87                                  1.010    F     CH.sub. 3  H   SCH.sub.3 181-187                                1.011    H     CH.sub.3   H   S(CH.sub.2).sub.2 CH.sub.3                                                               188-189                                1.012    Cl    CH.sub.3   H   SCH.sub.3 204-206                                ______________________________________                                    

    ______________________________________                                         Active ingredient table 2                                                       ##STR12##                     Ib                                              Compound                                                                       No.      R.sup.5                                                                              R.sup.6    R.sup.7                                                                             R.sup.8  mp(°)                           ______________________________________                                         2.001    H     CH.sub.3   H    H        160-168                                2.002    H     CH.sub.3   H    OCH.sub.3                                                                               150-151                                2.003    H     CH.sub.3   H    OCH.sub.2 CH.sub.3                                                                      150-152                                2.004    H     CH.sub.2 CH.sub.3                                                                         H    OCH.sub.3                                                                               147-149                                2.005    H     CH.sub.2 CH.sub.3                                                                         H    OCH.sub.2 CH.sub.3                                                                      130-132                                2.006    H     (CH.sub.2).sub.2 CH.sub.3                                                                 H    OCH.sub.3                                                                               200-202                                2.007    H     CH.sub.3   CH.sub.3                                                                            OCH.sub.3                                                                               137-139                                2.008    Cl    CH.sub.3   H    OCH.sub.3                                                                               208-211                                2.009    F     CH.sub.3   H    OCH.sub.3                                                                               179-182                                ______________________________________                                    

The herbicidal action of the N-[(6-trifluoromethylpyrimidin-2-yl)-aminocarbonyl]-2-carboalkoxybenzenesulfonamides of the formulae Ia and Ib on plant growth is demonstrated by the following greenhouse experiments:

The vessels employed were plastic flowerpots having a volume of 300 cm³ and filled with a sandy loam containing about 3.0% humus. The seeds of the test plants were sown separately, according to species.

For the preemergence treatment, the formulated active ingredients were applied to the surface of the soil immediately after the seeds had been sown. The compounds were emulsified or suspended in water as vehicle, and sprayed through finely distributing nozzles. The application rate was 0.03 kg of active ingredient per hectare. After the agents had been applied, the vessels were lightly sprinkler-irrigated to induce germination and growth. Transparent plastic covers were then placed on the vessels until the plants had taken root. The cover ensured uniform germination of the plants, insofar as this was not impaired by the active ingredients.

For the postemergence treatment, the plants were grown, depending on growth form, to a height of 3 to 15 cm before being treated. In this treatment method, either plants which had been sown in the pots and grown there were selected, or they were cultivated separately as seedlings and transplanted to the pots a few days before being treated. The application rates for postemergence treatment were 0.03 and 0.06 kg/ha. No covers were placed on the vessels in this method.

The pots were set up in the greenhouse, species from warmer climates in warmer areas (20° to 35° C.) and species from moderate climates at 10° to 20° C. The experiments were run for from 2 to 4 weeks. During this time the plants were tended and their reactions to the various treatments assessed. The assessment scale was 0 to 100, 100 denoting nonemergence or complete destruction of at least the visible plant parts, and 0 denoting no damage or normal growth.

The plants employed for the experiments were as follows:

    ______________________________________                                         Abbrev.                                                                               Botanical name  Common name                                             ______________________________________                                         ABUTH  Abutilon theophrasti                                                                           velvet leaf                                             AMARE  Amaranthus retroflexus                                                                         redroot pigweed                                         BROIN  Bromus inermis  smooth broome                                           CHEAL  Chenopodium album                                                                              lambsquarters (goosefoot)                               CYPIR  Cyperus iria    flatsedge, rice                                         ECHCG  Echinochlora crus-galli                                                                        barnyardgrass                                           GALAP  Galium aparine  catchweed bedstraw                                      LAMAM  Lamium amplexicaule                                                                            henbit                                                  POAAN  Poa annua       annual bluegrass                                        STEME  Stellaria media chickweed                                               VERSS  Veronica spp.   speedwell                                               ______________________________________                                    

For comparison purposes, compounds from U.S. Pat. No. 4,169,719 having the structure A or B were employed and compared with the novel active ingredients in which R¹ has a carbalkoxy structure.

    ______________________________________                                          ##STR13##                                                                     Comp. agent                                                                               R.sup.1 R.sup.2 Ex. in US-A 4,169,719                               ______________________________________                                         A          Cl      OCH.sub.3                                                                              Tab. I-E                                            B          Cl      CH.sub.3                                                                               Tab. I-D                                            ______________________________________                                    

Compounds 2.002 and 1.004, applied postemergence at rates of 0.03 and 0.06 kg/ha, had an excellent action on unwanted broadleaved plants, whereas A and B were virtually ineffective at these concentrations.

Compound 2.002, applied preemergence at a rate of 0.03 kg/ha, combated unwanted dicotyledonous and monocotyledonous plants very well; here again, A and B were virtually ineffective.

                                      TABLE A                                      __________________________________________________________________________     Control of unwanted broadleaved plants on postemergence application of         0.03 kg/ha in the greenhouse                                                    ##STR14##                                   I                                 Compound         Test plants and % damage                                      No.   R    R' (= R.sup.8)                                                                       CYPIR                                                                               ECHCG                                                                               ABUTH                                                                               AMARE                                                                               GALAP                                                                                VERSS                               __________________________________________________________________________     2.002 CO.sub.2 CH.sub.3                                                                   OCH.sub.3                                                                            100  98   98   100  100  100                                  A*    Cl   OCH.sub.3                                                                            0    0    0     0    0   0                                    B**   Cl   CH.sub.3                                                                             0    0    0    40   50   0                                    __________________________________________________________________________      A* = from USA 4,169,719 (Tab. IE)                                              B** = from USA 4,169,719 (Tab. ID)                                       

                                      TABLE B                                      __________________________________________________________________________     Control of unwanted broadleaved plants on preemergence application of          0.03 kg/ha in the greenhouse                                                    ##STR15##                                             I                                        Test plants and % damage                                      Compound                                                                             R    R' (= R.sup.8)                                                                       BROIN                                                                               ECHCG                                                                               POAAN                                                                               AMARE                                                                               CHEAL                                                                               GALAP                                                                                VERSS                                                                              CYPIR                      __________________________________________________________________________     2.002 CO.sub.2 CH.sub.3                                                                   OCH.sub.3                                                                            98   98   98   98   98   95   100  100                        A*    Cl   OCH.sub.3                                                                            0    0    0    0    0    0    0    0                          B**   Cl   CH.sub.3                                                                             0    0    0    0    0    0    0    0                          __________________________________________________________________________      A* = from USA 4,169,719 (Tab. IE)                                              B** = from USA 4,169,719 (Tab. ID)                                       

                  TABLE C                                                          ______________________________________                                         Control of unwanted broadleaved plants on postemergence application            of 0.06 kg/ha of active ingredient no. 1.004 in the greenhouse                  ##STR16##                                                                     Test plants   Damage in %                                                      ______________________________________                                         ABUTH         100                                                              AMARE         100                                                              CHEAL         100                                                              LAMAM         100                                                              STEME         100                                                              ______________________________________                                     

We claim:
 1. An N-((6-trifluoromethylpyrimidin-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamide of the formula Ia ##STR17## where the substituents have the following meanings: R¹ is hydrogen or halogen,R² is hydrogen, C₁ -C₅ -alkyl, C₃ -C₄ -alkenyl, C₃ -C₄ -alkynyl, C₁ -C₅ -haloalkyl, C₃ -C₅ -alkoxyalkyl, C₃ -C₅ -haloalkoxyalkyl or C₅ -C₆ -cycloalkyl, R³ is hydrogen, C₁ -C₂ -alkyl, allyl, propargyl or C₁ -C₅ -alkoxy, R⁴ is halogen, C₁ -C₂ -alkyl, C₁ -C₃ -alkylthio or C₁ -C₃ -alkylamino, with the proviso that R³ is not hydrogen or C₁ -C₂ -alkyl or C₁ -C₅ -alkoxy when R⁴ is halogen or C₁ -C₂ -alkyl, and their environmentally tolerated salts.
 2. An N-((6-trifluoromethlpyrimidin-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamide of the formula Ia as set forth in claim 1 where R² is methyl.
 3. A herbicidal composition containing a herbicidally effective amount of an N-((6-trifluoromethylpyrimidin-2-yl)aminocarbonyl)-2-carboalkoxybenzenesulfonamide of the formula Ia as set forth in claim 1, or an agriculturally useful salt thereof, and conventional auxiliaries or diluents.
 4. A process for combating unwanted plants, wherein a herbicidally effective amount of an N-((6-trifluoromethylpyrimidin-2-yl)aminocarbonyl)-2-carboalkoxybenzenesulfonamide of the formula Ia as set forth in claim 1, or an agriculturally useful salt thereof, is allowed to act on the plants and/or their habitat. 